Browse All Roscoe Village IL 5 Bedroom Properties for Sale

5 Beds ⋅ 4 Baths ⋅ 12753253 MLS ⋅ NEW Status

Set on a picturesque, tree-lined street in the sought-after Audubon School District, this beautifully appointed five-bedroom, 3.1-bath Roscoe Village residence delivers exceptional space, timeless character, and an effortless indoor-outdoor lifestyle. An elegant living room with a tray ceiling flows into the formal dining room, while rich hardwood floors, crown molding, custom millwork, and a striking iron-and-wood staircase add architectural distinction throughout. At the rear of the home, the expansive eat-in kitchen has been elevated with Taj Mahal quartzite countertops and backsplash, refinished maple cabinetry, updated hardware, stainless steel appliances, and a double-oven range. The kitchen opens seamlessly to an inviting family room anchored by a beautifully retiled fireplace, creating a sophisticated yet comfortable setting for everyday living and entertaining. French doors extend the space onto a large, sun-filled deck ideal for al fresco dining and relaxed summer gatherings. Three bedrooms occupy the upper level, including a serene primary retreat with soaring vaulted ceilings, skylights, a sleek linear gas fireplace, and a private balcony overlooking the backyard. The fully renovated primary bath offers a spa-like escape with a marble shower, soaking tub, heated porcelain tile floors, dual vanities, and refined lighting. Custom closet organizers, room-darkening shades, and refreshed flooring further enhance the home's comfort and functionality. The finished lower level provides exceptional flexibility with a spacious recreation room, two additional bedrooms, a full bath, and a convenient mudroom. Meticulously maintained and thoughtfully improved, the home also features updated patio doors, newer laundry appliances and water heater, an electric sump pump, recent masonry and tuckpointing, and updated HVAC systems. Complete with three fireplaces, multiple outdoor spaces, and a 2.5-car garage, this sophisticated residence offers gracious city living moments from the acclaimed dining, boutiques, and cafes along Roscoe Street, St. Benedict, the Paulina Brown Line, and near Hamlin Park.

3242 N Leavitt Street, Chicago

$6,500,000

5 Beds ⋅ 6 Baths ⋅ 12719016 MLS ⋅ ACTIVE Status

Situated in the absolute heart of Roscoe Village, this distinguished corner church has been spectacularly converted into a sprawling single-family estate. The handsome red-brick building spans over two city lots and offers approximately 10,000 square feet of magnificent living space. Despite its grand scale, the home is designed to feel remarkably private and surprisingly intimate. The property features 5 bedrooms, 4 full baths, 2 half baths, and 2 kitchens. The definitive highlight is the former nave, transformed into one of the most spectacular living rooms in Chicago, complete with 25-foot vaulted ceilings and original beams and woodwork. Natural light fills the room, filtered by the breathtaking restored stained glass windows. New herringbone quarter sawn oak floors are stunning throughout. The striking bell tower is accessible via an interior staircase that provides sweeping neighborhood views. The main level kitchen features a mix of new and retrofitted antique cabinetry, chef's appliances, and abundant storage. The dining room opens to a private rooftop terrace tucked nicely behind the crenellated parapet wall. Three guest bedrooms are located in their own wing; one en-suite and the other two sharing a bathroom. One of the bedrooms, currently configured as an office, features a breathtaking fireplace. Rooms are spacious and private, offering fantastic natural light. The primary suite is sprawling with vaulted ceilings, multiple sitting areas, 2 large walk-in closets, a laundry setup, and a large bathroom with a separate tub and shower. It's truly a home within a home. The lower level offers a massive family room with a wet bar, catering kitchen, and mud room leading to the attached two-car garage. There is also a large gallery leading to the guest suite, which has an en-suite bathroom and separate entrance, making it the perfect private retreat. Several efficient mechanical systems keep the house comfortable year round including sub-slab radiant heat and beautiful historical radiators. The well-planned systems create a living environment that is both comfortable and efficient. The location is perfect, just steps to Roscoe Village dining and shopping along Damen, Lincoln, and Roscoe. Located in the Audubon school district and just steps to the Paulina Brown Line station.

1901 W Cornelia Avenue, Chicago

$1,250,000

5 Beds ⋅ 4 Baths ⋅ 12711940 MLS ⋅ CONTINGENT Status

This is a rare opportunity to own a legal 3-unit building in the heart of Roscoe Village. Featuring a stately facade and impressive curb appeal, the property sits on a beautiful, tree-lined block in one of Chicago's most desirable neighborhoods-offering the perfect blend of stability and upside for investors or owner-occupants alike. Each unit offers a well-designed layout with in-unit washer and dryer, individual heating and cooling expenses, separate hot water tanks, and private outdoor space-highly desirable features that attract and retain quality tenants. The building is consistently easy to rent, with thoughtfully structured leases that include detailed riders and built-in rent increases. As leases turn over, there is additional opportunity to further enhance income, as they are currently rented below market value. Rents listed are estimated market values. Current rents are $2695 for unit 1, $2375 for unit 2 including parking, and $2790 for unit 3, plus $165/month for the additional parking spot. The property also includes a backyard and a 2-car garage. For those seeking an owner-occupied option, the unique two-level top-floor unit presents an exceptional opportunity to live comfortably while generating income below.

1742 W School Street, Chicago

$1,750,000

5 Beds ⋅ 5 Baths ⋅ 12462111 MLS ⋅ PENDING Status

2237 W Roscoe Street Unit #2W, Chicago

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